Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

…, A Matsubara, T Nemoto, M Saito, S Hirayama…

Index: Ida, Yoshihiro; Matsubara, Ayaka; Nemoto, Toru; Saito, Manabu; Hirayama, Shigeto; Fujii, Hideaki; Nagase, Hiroshi Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 19 p. 5810 - 5831

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Citation Number: 10

Abstract

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (−)-TAN-67 in the acetic acid writhing test. This study of the structure–activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′-or 8′- ...

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2-Amino-4-metho...

~64%

2-AMINO-4-METHOXYBENZYL ALCOHOL Structure

187731-65-3

2-AMINO-4-METHO...

(2-Amino-5-fluorophenyl)methanol Structure

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(2-Amino-5-fluo...

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2-Amino-5-fluorobenzaldehyde Structure

146829-56-3

2-Amino-5-fluor...

2-Amino-5-fluorobenzoic acid Structure

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2-Amino-5-fluor...

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2-Amino-5-fluorobenzaldehyde Structure

146829-56-3

2-Amino-5-fluor...

2-Amino-4-nitrobenzoic acid Structure

619-17-0

2-Amino-4-nitro...

~91%

2-Amino-4-nitrobenzenemethanol Structure

78468-34-5

2-Amino-4-nitro...

2-AMINO-4-METHOXYBENZYL ALCOHOL Structure

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2-AMINO-4-METHO...

~74%

Benzaldehyde,2-amino-4-methoxy- Structure

59236-36-1

Benzaldehyde,2-...

2-Amino-4-methoxybenzoic acid Structure

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2-Amino-4-metho...

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Benzaldehyde,2-amino-4-methoxy- Structure

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Benzaldehyde,2-...

2-Amino-3-methoxybenzoic acid Structure

3177-80-8

2-Amino-3-metho...

~97%

(2-Amino-3-methoxyphenyl)methanol Structure

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2-amino-3-methylbenzyl alcohol Structure

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2-Amino-3-methylbenzaldehyde Structure

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2-Amino-6-chlorobenzoic acid Structure

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(2-Amino-6-chlorophenyl)methanol Structure

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55414-72-7

(2-Amino-5-meth...

~58%

Benzaldehyde,2-amino-5-methoxy- Structure

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2-Amino-5-methoxybenzoic acid Structure

6705-03-9

2-Amino-5-metho...

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Benzaldehyde,2-amino-5-methoxy- Structure

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(2-Amino-4-(trifluoromethyl)phenyl)methanol Structure

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2-amino-4-(trifluoromethyl)benzaldehyde Structure

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4-Trifluoromethylanthranilic acid Structure

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2-amino-4-(trifluoromethyl)benzaldehyde Structure

109466-88-8

2-amino-4-(trif...

2-Amino-5-(trifluoromethyl)benzoic acid Structure

83265-53-6

2-Amino-5-(trif...

~87%

[2-Amino-5-(trifluoromethyl)phenyl]methanol Structure

220107-65-3

[2-Amino-5-(tri...

2-Amino-4-fluorobenzoic acid Structure

446-32-2

2-Amino-4-fluor...

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2-AMINO-4-FLUOROBENZYL ALCOHOL Structure

197783-88-3

2-AMINO-4-FLUOR...

(2-Amino-3-chlorophenyl)methanol Structure

61487-25-0

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2-Amino-3-chlorobenzaldehyde Structure

397322-82-6

2-Amino-3-chlor...

2-Amino-3-chlorobenzoic acid Structure

6388-47-2

2-Amino-3-chlor...

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2-Amino-3-chlorobenzaldehyde Structure

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2-Amino-3-chlor...

2-Amino-3-fluorobenzoic acid Structure

825-22-9

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2-amino-3-fluorobenzaldehyde Structure

854538-94-6

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2-Amino-3-methoxybenzaldehyde Structure

70127-96-7

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2-Amino-3-nitrobenzoic acid Structure

606-18-8

2-Amino-3-nitro...

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2-Amino-6-nitrobenzoic acid Structure

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(2-Amino-6-nitrophenyl)methanol Structure

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2-Amino-5-nitro...

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Benzaldehyde,2-amino-5-nitro- Structure

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Benzaldehyde,2-...

Benzenemethanol, 2-amino-6-methoxy- (9CI) Structure

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4-METHYL-2-NITROBENZYLALCOHOL Structure

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4-METHYL-2-NITR...

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2-amino-4-methylbenzaldehyde Structure

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Benzoic acid,4-methyl-2-nitro- Structure

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2-amino-4-methylbenzaldehyde Structure

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2-amino-6-chlorobenzaldehyde Structure

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